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Additional Problem Set CH10-12

Additional Problem Set CH10-12 - provide reagents for the...

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Additional Problem Set. Chapters 10-11. Conceptual Questions. 1. The molecule below is expected to be a poor hydroboration reagent of double bonds. Explain why by discussing the most important frontier orbital interactions in the transition state. O B O H 2. In the mechanism of oxidation of trialkylboranes we showed a rearrangement raction where OH was a leaving group. Write out the mechanism for triethylborane oxidation by H 2 O 2 in base and explain why OH - can be a leaving group. 3. Alkyne π -bonds are less reactive (that is more stable) than alkene π -bonds. Explain why.
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Identification # ___ ___ ___ ___ 1 Mechanistic Questions. 4. By drawing the mechanism please explain the products of the following reactions. In the third reaction
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Unformatted text preview: provide reagents for the transformation. O TsOH/H 2 O MeOH O OMe BH 2 B ? N 3 5. By showing the mechanism explain the transformation below. HO O I 2 NaOH O O I 6. Compound A is hydrogenated faster than compound B using H2/Pd-C. Explain why. A B Identification # ___ ___ ___ ___ 2 Synthesis Questions. 7. Starting with acetylene synthesize the following epoxide in four steps. O 8. Devise a two-step synthesis of the alcohol below. Explain why hydroboration-oxidation cannot be used to directly form the alcohol in one step. OH...
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